Inclusion compound design: the piedfort concept

Jessiman, Alan S.; MacNicol, David D.; Mallinson, P. R.; Vallance, Ian

doi:10.1039/c39900001619

Cited by 51 publications

(38 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The resulting crystal structure shows that the double‐deckers adopt the desired C 3 h symmetry, and that the monomers are arranged in layers, in which the triazine units of the monomers stack densely above each other, always rotated by 60°. This hexagonal composite unit of two monomers beautifully exemplifies the Piedfort concept 14. The anthracene blades of neighboring compounds are stacked edge‐to‐face (etf).…”

Section: Resultsmentioning

confidence: 83%

Facile Synthesis and Theoretical Conformation Analysis of a Triazine‐Based Double‐Decker Rotor Molecule with Three Anthracene Blades

Kory

Bergeler

Reiher

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

The facile synthesis of a rotor-shaped compound with two stacked triazine units, which are symmetrically connected by three anthracene blades through oxygen linkers, is presented. This new double-decker, which is a potential monomer for two-dimensional polymerization, was synthesized by using readily available, cheap building blocks, exploiting the known selectivity difference for the nucleophilic substitution of cyanuric chloride. The crystal structure of a C3h symmetric rotor-shaped compound with 9,10-dihydroanthracene blades, which is a direct precursor to the targeted monomer, and the crystal structure of the new double-decker with the desired C3h symmetry, are also reported. The synthetic efforts were preceded by a computational analysis, which was triggered by the question of conformational stability of the potential monomer. Two stable conformers could be found, and the barrier for the transition path in the gas phase between these conformers was determined by quantum chemical calculations. Exploratory Born-Oppenheimer molecular-dynamics simulations revealed a strong influence of solvent-solute interactions on the stability of the conformers, which resulted in an energetic preference of the C3h symmetric conformation of the double-decker.

show abstract

Section: Resultsmentioning

confidence: 83%

Facile Synthesis and Theoretical Conformation Analysis of a Triazine‐Based Double‐Decker Rotor Molecule with Three Anthracene Blades

Kory

Bergeler

Reiher

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…It seems that in this particular molecule an acceptable compromise is found between void space, concatenation of molecules and inclusion of guests. The formation of a bilayer structure in compound 1 is reminiscent of the Piedfort units observed in other C 3 -symmetric systems like 2,4,6-tris[4-(2-phenylpropan-2-yl)phenoxy]-1,3,5-triazine, 11 in which two p-stacked molecules are mutually rotating by 60° to resemble a spatially filled hexagonal system. This work was supported in part by the Netherlands Foundation of Chemical Research (SON) with financial aid from the Netherlands Organization for Scientific Research (NWO).…”

Section: Take Down Policymentioning

confidence: 90%

Hydrogen-bonded porous solid derived from trimesic amide

Palmans

Vekemans

Kooijman³

et al. 1997

Chem. Commun.

View full text Add to dashboard Cite

“…The Piedfort Unit dimer (PU) [30][31][32] is stabilized by π ••• π stacking (3.34Å) and C H ••• O and C H ••• N interactions from the ortho-phenyl donor to the phenoxytriazine group of the next layer. The ortho-halogen on both sides prevents continuous stacks along the PU axis, and so the molecules align with slight offset.…”

Section: Structural Analysismentioning

confidence: 99%